Benzyl Bromide → 1-(Benzyloxy)-2-bromo-4-chlorobenzene

HRID 1694692Notes

Reaction equation

HRID 1694692 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:9][C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1[OH:17].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:9][C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1[O:17][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 696702-Bromo-4-chlorophenol

Product 1

HCID 115511251-(Benzyloxy)-2-bromo-4-chlorobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzyl bromide (13.1 ml) was added to a stirred mixture of 2-bromo-4-chlorophenol (20.7 g) and potassium carbonate (27.6 g) in DMF (200 ml). After 72 h, the mixture was partitioned between diethylether and water, the organic layer washed with water, dried and the solvent evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 2% EtOAc/isohexane. Yield 18.1 g

Workup

  1. customthe mixture was partitioned between diethylether and water
  2. washthe organic layer washed with water
  3. customdried
  4. customthe solvent evaporated under reduced pressure
  5. customThe residue was purified by chromatography on silica eluting with 2% EtOAc/isohexane

Sources & evidence

ORD record
ord-b3fcaffc0317480c863e1ba8895ab7a0
Source dataset
uspto-grants-2012_04
Patent number
US08158820B2

Reaction notes

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